Dicarbon monoxide

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Dicarbon monoxide
Stick model of dicarbon monoxide
Spacefill model of dicarbon monoxide
Ball and stick model of dicarbon monoxide
Names
IUPAC name
2-Oxoethenylidene
Other names
Ketenylidene
Identifiers
  • 119754-08-4 ☑Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 164756 ☑Y
PubChem CID
  • 189691
Properties
C2O
Molar mass 40.02 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☑Y verify (what is ☑Y☒N ?)
Infobox references

Dicarbon monoxide (C2O) is a molecule that contains two carbon atoms and one oxygen atom. It is a linear molecule that, because of its simplicity, is of interest in a variety of areas. It is, however, so extremely reactive that it is not encountered in everyday life. It is classified as a cumulene and an oxocarbon.[1]

Occurrence

Dicarbon monoxide is a product of the photolysis of carbon suboxide:[2][3]

C3O2 → CO + C2O

It is stable enough to observe reactions with NO and NO2.[4]

Called ketenylidene in organometallic chemistry, it is a ligand observed in metal carbonyl clusters, e.g. [OC2Co3(CO)9]+. Ketenylidenes are proposed as intermediates in the chain growth mechanism of the Fischer-Tropsch Process, which converts carbon monoxide and hydrogen to hydrocarbon fuels.[5]

The organophosphorus compound (C6H5)3PCCO (CAS# 15596-07-3) contains the C2O functionality. Sometimes called Bestmann's Ylide, it is a yellow solid.[6]

References

  1. ^ Frenking, Gernot; Tonner, Ralf "Divalent carbon(0) compounds" Pure and Applied Chemistry 2009, vol. 81, pp. 597-614. doi:10.1351/PAC-CON-08-11-03
  2. ^ Bayes, K. (1961). "Photolysis of Carbon Suboxide". Journal of the American Chemical Society. 83 (17): 3712–3713. doi:10.1021/ja01478a033. 
  3. ^ Anderson, D. J.; Rosenfeld, R. N. (1991). "Photodissociation of Carbon Suboxide". Journal of Chemical Physics. 94 (12): 7857–7867. doi:10.1063/1.460121. 
  4. ^ Thweatt, W. D.; Erickson, M. A.; Hershberger, J. F. (2004). "Kinetics of the CCO + NO and CCO + NO2 reactions". Journal of Physical Chemistry A. 108 (1): 74–79. doi:10.1021/jp0304125. 
  5. ^ Jensen, Michael P.; Shriver, Duward F. "Carbon-carbon and carbonyl transformations in ketenylidene cluster compounds" Journal of Molecular Catalysis 1992, vol. 74, pp. 73-84. doi:10.1016/0304-5102(92)80225-6
  6. ^ H. J. Bestmann, R. Zimmermann, M. Riou "Ketenylidenetriphenylphosphorane" e-EROS Encyclopedia of Reagents for Organic Synthesis 2001. doi: 10.1002/047084289X.rk005.pub2


Retrieved from "https://en.wikipedia.org/w/index.php?title=Dicarbon_monoxide&oldid=852134020"
This content was retrieved from Wikipedia : http://en.wikipedia.org/wiki/Dicarbon_monoxide
This page is based on the copyrighted Wikipedia article "Dicarbon monoxide"; it is used under the Creative Commons Attribution-ShareAlike 3.0 Unported License (CC-BY-SA). You may redistribute it, verbatim or modified, providing that you comply with the terms of the CC-BY-SA